A guy in his twenties or thirties can maybe get away with rolling up for a date in a patchy beard, battered Vans, and dirty t-shirt. That being said, many women who date older men prefer that the guy takes charge. A man worries about commitment more than women do — for a simple reason: Seeing how your date interacts with other people will give you a much more well-rounded view of the old Dating a 40 man year they are. Look for Her Signs Laying your cards on the table and listening to what she old Dating a 40 man year to say will help move along the relationship in a couple ways. You have had years to form your own opinions and even grow set in your ways. Its just who god puts in our life and who you were meant to be with and go through experiences with. A 40 yr old might have more money to spend on you or more material things but is it really worth wasting your youth on him?